Functionalization method for nitrogenous heterocyclic compound
A nitrogen heterocyclic compound, functional group technology, applied in the direction of organic chemistry, can solve the problems of high reaction temperature, narrow substrate expansion range, waste of time and money, etc., to overcome the problems of high temperature, simple operation, and mild reaction conditions Effect
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Embodiment 1
[0020] Taking the preparation of 2-(4-methoxyphenyl)-4-(trifluoromethyl)pyridine as an example, its structural formula is shown below, and the raw materials used and the preparation method are as follows:
[0021]
[0022] 1. Preparation of p-methoxyphenyl diazonium salt
[0023] Add 1.23g of p-methoxyaniline into a 100mL round bottom flask, add 4mL of distilled water and 3.4mL of fluoroboric acid aqueous solution with a mass fraction of 50%, stir until the solution is transparent, cool in an ice-salt bath, and dissolve 0.69g of sodium nitrite Dissolve in 1.5mL distilled water, drop it into a round bottom flask with a syringe at a rate of 1-2 drops / second, stir and react at 0°C for 40 minutes, suction filter with a Buchner funnel, and then reconstitute with acetone and anhydrous ether Crystallized to obtain a white solid, which was dried naturally to prepare p-methoxyphenyl diazonium salt.
[0024] 2. Functionalization of trifluoromethylpyridine
[0025] Under argon prote...
Embodiment 2
[0027] Taking the preparation of 4-chloro-2-(4-methoxyphenyl)pyridine as an example, its structural formula is shown below, and the raw materials used and the preparation method are as follows:
[0028]
[0029] In the functionalization step 2 of the nitrogen-containing heterocyclic compound in Example 1, under the protection of argon, 67 mg (0.3 mmol) of p-methoxyphenyl diazonium salt, 1341 mg (9 mmol) of p-chloropyridine hydrochloride, Dichloride-tris-bipyridine ruthenium 5.6mg (0.0075mmol) was placed in a 10mL reaction tube, and p-methoxyphenyl diazonium salt was combined with p-chloropyridine hydrochloride and dichloride-tris-bipyridine The molar ratio of ruthenium is 1:30:0.025, and 1 mL of distilled water is added, and other steps of this step are the same as in Example 1. Other steps are the same as in Example 1, and the light yellow oily liquid 4-chloro-2-(4-methoxyphenyl)pyridine is prepared, the yield is 68%, and the spectral data of the product is: 1 H NMR (400M...
Embodiment 3
[0031] Taking the preparation of 2-(4-methoxyphenyl) quinoline as an example, its structural formula is as follows, and the raw materials used and the preparation method are as follows:
[0032]
[0033] In the functionalization step 2 of the nitrogen-containing heterocyclic compound in Example 1, under the protection of argon, 67 mg (0.3 mmol) of p-methoxyphenyl diazonium salt, 1485 mg (9 mmol) of quinoline hydrochloride, and di Chloride-three-bipyridyl ruthenium 5.6mg (0.0075mmol) is placed in a 10mL reaction tube, and the mixture of p-methoxyphenyl diazonium salt and quinoline hydrochloride, dichloride-three-bipyridine ruthenium The molar ratio was 1:30:0.025, 1 mL of distilled water was added, and the other steps of this step were the same as in Example 1. Other steps are identical with embodiment 1, are prepared into light yellow solid 2-(4-methoxyphenyl) quinoline, and its productive rate is 60%, and the spectral data of product is:1 H NMR (400MHz, CDCl 3 )δ8.14-8.19...
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